Chemoselectivity and the Chan-Lam Coupling Reaction: Adding Amino Acids to Polymer-Coated Microelectrode Arrays

Matthew D. Graaf, Kevin D. Moeller

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

(Chemical Equation Presented). The placement of a peptide onto a microelectrode array is frequently complicated by the presence of multiple nucleophiles in the peptide. In the work reported here, we have found that the Chan-Lam coupling reactions used to site-selectively place thiol, alcohol, and amine nucleophiles onto diblock-copolymer-coated surfaces are chemoselective for the placement of thiol and alcohol nucleophiles on the arrays. This means that cysteine- and serine-containing peptides can be placed onto an array without any need to protect the N terminus of the peptide. Furthermore, it was found that placement of thiol groups onto an array with the Chan-Lam reaction using optimized reaction times leads to complete coverage of the electrodes. The extent of this coverage can be controlled by varying the reaction time in a manner that allows for the construction of arrays with a gradient of peptide concentrations.

Original languageEnglish
Pages (from-to)1527-1534
Number of pages8
JournalJournal of Organic Chemistry
Volume81
Issue number4
DOIs
StatePublished - Feb 19 2016

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